Selah Sue wears Dolce & Gabbana silk-blend dress. Eddie Borgo cuff (right wrist) and bangle (left wrist); A-Morir sunglasses. Click here to view the slideshow.

Between her signature slapdash bouffant—a style she’s sported daily since age 14—and her smoky blues-based vocals, Selah Sue can’t seem to escape the Amy Winehouse comparisons. “I’m not sad about it,” says the 23-year-old Belgian. “But if you listen to my music, it’s very different.” Indeed, her funky neo-soul repertoire, which has earned accolades from the likes of Prince and Cee Lo Green, is riddled with more Jamaican rhythms than Motown sound, but there is no denying its lineage. The modernized-midcentury vibe that Winehouse made cool nearly a decade ago—and Adele subsequently brought to the mainstream—still resonates with many of today’s up-and-coming musicians. And fashion seems to be having a love affair with that era as well. In this portfolio, the season’s fifties- and sixties-inspired looks are the perfect fit for five rising talents, all of whom are putting their own spin on retro sounds. In the pack: Binki Shapiro and Adam Green, two indie-rock darlings who together are turning out woozy pop in the style of Nancy Sinatra and Lee Hazlewood; Bosco Delrey, a New Jersey boy with a Bob Dylan ’do making catchy tunes drenched in Memphis blues; and Lianne La Havas, a young Londoner who dresses like a fifties schoolgirl— and sings like a fifties soul diva.

Hair by Jimo Salako at MFA; makeup by Mathias van Hooff for MAC Cosmetics at MFA; manicure by Marian Newman at Streeters London. Production by Shiny Projects; set design by Gillian O’Brien at MFA; digital technician: Nick Dehadray at Numerique. Photography assistants: Ed Singleton, Lindsay Watson, Oliver Holms, Matt Lain. Fashion assistants: Solange Franklin, Hannah Clarke, Otter Hatchett. Special thanks to Loft Studios and Film Plus.